The burden of chronic illness is greater in many developing countries, where households have limited access to formal insurance mechanisms. Despite its significance in the welfare of people in developing countries, studies have rarely investigated the effects of chronic illness on aspirations, the failure of which may be reciprocally linked to a self-sustaining trap of poverty. Using two waves of Indonesian Family Life Survey (IFLS 2007, 2014), this paper examines the effect of chronic illness on aspirations and the channel through which the duration of chronic illness affects aspirations and subjective wellbeing (SWB). To this end, this paper uses a variable measuring an aspirations gap, constructed by a difference between an individual’s current level of SWB and her future aspired level of wellbeing. This study finds no evidence that chronic illness affects the aspired level of future wellbeing. Instead, the results show that the aspirations gap increases while the current SWB deteriorates over the duration of chronic illness. Moreover, the findings show that the emotional wellbeing of individuals with chronic illnesses decreases as the duration of chronic conditions increases, especially in low income households. Overall, the results of this study suggest that chronic illness brings about a vicious cycle in which a deterioration in current SWB leads to a greater aspirations gap, which, in turn, reinforces feelings of unhappiness and dissatisfaction with life in Indonesia.